Rodriguesic Acids, Modified Diketopiperazines from the Gastropod Mollusc<i>Pleurobranchus areolatus</i>

Pereira, Fábio Renato; Santos, Mário F. C.; Williams, David E.; Andersen, Raymond J.; Padula, Vinícius; Ferreira, Antônio G.; Berlinck, Roberto G. S.

doi:10.5935/0103-5053.20140037

Cited by 4 publications

(7 citation statements)

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“…New diketopiperazines 1303-1306 were reported from Pleurobranchus areolatusrelated metabolites have been reported from the ascidian Didemnum sp., a suspected prey of P. areolatus. 805 Further investigation into the origin of tetrodotoxin in Pleurobranchaea maculata demonstrated that the mollusc can accumulate the toxin through its diet however there was no identiable tetrodotoxin source in the molluscs local environment. 806 Two studies of sea hares identied two moderately cytotoxic sesquiterpenes oculiferane 1307 and epi-obtusane 1308 (Aplysia oculifera) 807 and an anti-neuroinammatory diterpene dactyloditerpenol acetate 1309 (A. dactylomela).…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2016

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This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2016

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“…Such a wide occurrence of natural products in taxonomically unrelated phyla is often indicative of a microbial origin. Indeed, DKPs have been reported from marine fungi, yeast, and bacteria, including actinobacteria [ 34 , 35 , 36 , 37 ]. There have been many reports on the isolation of DKPs from sponges [ 16 , 37 ].…”

Section: Discussionmentioning

confidence: 99%

“…There have been many reports on the isolation of DKPs from sponges [ 16 , 37 ]. DKP hydroxamates (DKPHs) are relatively uncommon in nature and have been isolated from tunicates and mollusks with promising antifungal activity [ 20 , 36 ]. Etzionin belongs to the DKPH family and was originally reported from an unidentified tunicate from the Gulf of Eilat (the Red Sea) [ 20 ].…”

Section: Discussionmentioning

confidence: 99%

“…Etzionin belongs to the DKPH family and was originally reported from an unidentified tunicate from the Gulf of Eilat (the Red Sea) [ 20 ]. Etzionin is structurally closer to rodriguesic acids and rodriguesins A and B that were isolated from the gastropod mollusk Pleurobranchus areolatus and the ascidian Didemnum sp., respectively [ 19 , 36 ]. In this study, for the first time, we isolated and characterized etzionin, as well as its two new derivatives, from a marine sponge.…”

Section: Discussionmentioning

confidence: 99%

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Molecular Networking-Guided Isolation of New Etzionin-Type Diketopiperazine Hydroxamates from the Persian Gulf Sponge Cliona celata

Kouchaksaraee

Nazemi

et al. 2021

Marine Drugs

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The Persian Gulf is a unique and biologically diverse marine environment dominated by invertebrates. In continuation of our research interest in the chemistry and biological activity of marine sponges from the Persian Gulf, we selected the excavating sponge Cliona celata for detailed metabolome analyses, in vitro bioactivity screening, and chemical isolation studies. A UPLC-MS/MS (MS2) molecular-networking-based dereplication strategy allowed annotation and structural prediction of various diketopiperazines (DKPs) and etzionin-type diketopiperazine hydroxamates (DKPHs) in the crude sponge extract. The molecular-networking-guided isolation approach applied to the crude extract afforded the DKPH etzionin (1) and its two new derivatives, clioetzionin A (2) and clioetzionin B (3). Another new modified DKP (4) was identified by MS/MS analyses but could not be isolated in sufficient quantities to confirm its structure. The chemical characterization of the purified DKPHs 1–3 was performed by a combination of 1D and 2D NMR spectroscopy, HRMS, HRMS/MS, and [α]D analyses. Compounds 1 and 2 exhibited broad antibacterial, antifungal, and anticancer activities, with IC50 values ranging from 19.6 to 159.1 µM. This is the first study investigating the chemical constituents of a C. celata specimen from the Persian Gulf. It is also the first report of full spectroscopic data of etzionin based on extensive spectroscopic analyses.

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“…Rodriguesic acid (55), rodriguesic acid hydroxamate (56), and their methyl esters 57 and 58, featured as diketopiperazine skeletons, were isolated from the heterobranch mollusk Pleurobranchus areolatus (Ilha do Papagaio, Cabo Frio, Rio de Janeiro state) by Berlinck et al 74 RP C 18 -silica-gel column, HPLC-UV-MS analysis, phenyl-derivatized silica gel column and RP HPLC were combined to obtain these diketopiperazines. The isolation of rodriguesic acid (55) as its corresponding ammonium salt was indicated by the integration of the NH 3 + signal at d 7.63, as well as the fact that CH 2 -14 was observed as a sextet in its 1 H-NMR spectrum.…”

Section: Diketopiperazinesmentioning

confidence: 99%